Methyl Isocyanate → HCID 57063098, compound

HRID 1650271Notes

Reaction equation

HRID 1650271 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH:13]=[C:14]([CH3:18])[C:15](=[O:17])[CH3:16])=[O:6])[CH:2]=[CH2:3].[CH3:19][N:20]=[C:21]=[O:22]>N1C=CC=CC=1>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][C:21](=[O:22])[NH:20][CH3:19])[CH2:9][C@H:8]1[CH:13]=[C:14]([CH3:18])[C:15](=[O:17])[CH3:16])=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 57026776HCID 57026776, compound

Product 1

HCID 57063098HCID 57063098, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of (2S,4R)-1-allyloxycarbonyl-4-hydroxy-2-(2-methyl-3-oxo-1-butenyl)pyrrolidine (1.35 g) and methyl isocyanate (0.31 ml) was added a drop of pyridine. The resulting mixture was allowed to stand at ambient temperature for 2 days. Evaporation of the mixture gave a residue, which was chromatographed on silica gel (60 ml) eluting with a mixture of n-hexane and ethyl acetate (1:1 V/V) to give (2S,4R)-1-allyloxycarbonyl-4-(methylcarbamoyloxy)-2-(2-methyl-3-oxo-1-butenyl)pyrrolidine (1.60 g).

Workup

  1. customEvaporation of the mixture
  2. customgave a residue, which
  3. customwas chromatographed on silica gel (60 ml)
  4. washeluting with a mixture of n-hexane and ethyl acetate (1:1 V/V)

Sources & evidence

ORD record
ord-f2cddc2cae174144959f163ef001119a
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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